Smoking-friendly holiday rentals in The Berkshires

Staying at Robert’s place was such a great experience. The property was beautiful, and the surrounding area was calm and scenic making it feel like a perfect getaway. Robert was super responsive and easy to talk to, which made everything smooth from start to finish. It was really nice meeting him in person—he even greeted us in Swedish and gave us a little tour of the place, which made us feel extra welcome. We look forward to come visit again to explore the area more!

This was our second stay at Shawn's property in Wilmington, and once again, it exceeded our expectations. The accommodations were perfect for our needs, and we had a wonderful time. During our stay, we experienced a snowstorm, but Shawn was proactive in ensuring the entrance was cleared promptly, allowing us to come and go without any issues. His attention to detail and commitment to making our stay enjoyable truly stood out. We greatly appreciate his hospitality and look forward to returning in the future. Thank you again for such a memorable stay!

We had a perfect family time at Susie’s fun farmhouse! The very clean bathroom and nice beds made us feel comfortable. We spent a lot of time with friendly farm pets all day, it was a wonderful experience. Susie is a super host! She is funny and friendly and we all love her so much. Can’t wait to come back soon:)

Mariann has a great space in a great location. Very accommodating and friendly, made you feel very welcome . Very responsive. Really nice area. Would highly recommend.

Jennifer and Jodi were amazing hosts. the space was clean, large, and had a great view, and we even got to hang out with the cats a little bit! bit! location was great, for everything we wanted to do for the weekend, we didn't have to drive more than 20 minutes. we would definitely stay here again given the chance.

Stayed here for a couple months, while waiting to close on my house. Peter and Adam, we’re both helpful and prompt with questions and responses. Walking trails within a mile or so, lots of restaurants and stores within 2-4 miles. Would definitely stay here again.

We had a wonderful stay on Gemma’s property and felt right at home. The kids loved feeding the farm animals — a total highlight!! Gemma generously provided us with an array of breakfast items, which really made for lovely mornings. We would absolutely return!

Great setup and location with everything was easily walkable and with the parking pass made it easy to leave during the day and still have a place to park.

Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

I needed a place on very short notice that could house my bunny, and the cabin was perfect.

We were 6 adults and 4 young kids, and everyone had a fantastic time at Twin Peaks! The house is up in the mountains a bit, in a clearing surrounded by forest, overlooking the valley below, and both the house and property have a great feel. The views - especially from the great room - are reason enough stay here, but the house compliments the views nicely. Well laid out, nice flow, two working fireplaces, comfy rugs/carpets throughout, cool decor, comfortable beds, big finished basement for the kids. We hung out in every room, watched a few movies, cooked good meals, used the outdoor grill, hiked in the state recreation area behind the house, enjoyed watching the deer and turkeys, had fires in the outdoor fire pit, and had a great day of sledding right in front of the house. We also loved skiing at Plattekill Mountain, which is only 10 minutes away. I highly recommend Twin Peaks!

Felt right at home ! Was so peaceful and the view & surroundings were absolutely beautiful! Loved every moment being there. On our last day there, it ended up snowing so we got to enjoy the sledding. Was amazing! Would come back again without hesitation and would definitely recommend to friends & family! Jeff was a wonderful host & anyone who books at this place, YOU WONT REGRET IT ! :)

What a wonderful stay we had at the beautiful Queens cottage! The place was spotlessly clean. The house manual was great and even included itineraries for the area. We loved the snacks that were left for guests. The main bathroom was spa-like and all the beds were comfortable. Our only complaint was that the place was so amazing we did not want to leave!!

Didn’t want to leave! The place was very cozy, we felt right at home and the sound of the creek in the background was the cherry on top! You sleep peacefully on comfortable bedding and get to cook great meals in a cozy kitchen and enjoy a walk in the morning to the nearby waterfall! Sunsets were spent lazily on the hammock socking up the sun and fresh air. At night, we really enjoyed watching Nteflix on the projector screen and catching up.

We loved our stay at this house , great location to move around the Catskills mountains. Our Girls were really happy playing at the Garden, doing marshmellows on the fire every day and off course using the hot tub!

Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!

This is a wonderful stay in a cozy private room. The hosts were incredibly kind and welcoming and made me feel right at home. The room itself was very comfortable and well-appointed. I was encouraged to use the shared spaces, such as the living room and kitchen, which added to the warm and inviting atmosphere. I’d recommend this listing if you’re looking for a friendly and comfortable stay.